US4699983A - 2-amino-4-trichloromethylpyridine and its preparation - Google Patents

2-amino-4-trichloromethylpyridine and its preparation Download PDF

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Publication number
US4699983A
US4699983A US06/838,780 US83878086A US4699983A US 4699983 A US4699983 A US 4699983A US 83878086 A US83878086 A US 83878086A US 4699983 A US4699983 A US 4699983A
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US
United States
Prior art keywords
amino
trichloromethylpyridine
soil
added
preparation
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Expired - Fee Related
Application number
US06/838,780
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English (en)
Inventor
Helmut Hagen
Hans Ziegler
Rolf-Dieter Kohler
Ernst-Heinrich Pommer
Jurgen Dressel
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BASF SE
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BASF SE
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Assigned to BASF AKTIENGESELLSCHAFT reassignment BASF AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: DRESSEL, JUERGEN, HAGEN, HELMUT, KOHLER, ROLF-DIETER, POMMER, ERNST-HEINRICH, ZIEGLER, HANS
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
    • C05G3/90—Mixtures of one or more fertilisers with additives not having a specially fertilising activity for affecting the nitrification of ammonium compounds or urea in the soil
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
    • Y02P60/20—Reduction of greenhouse gas [GHG] emissions in agriculture, e.g. CO2
    • Y02P60/21—Dinitrogen oxide [N2O], e.g. using aquaponics, hydroponics or efficiency measures

Definitions

  • 2-Chloro-6-trichloromethylpyridine is known to be a nitrification inhibitor; the common name of the active ingredient is nitrapyrin. Its preparation and action are described in, for example, U.S. Pat. No. 3,135,594.
  • Aminohalopyridines are also known substances. Although they have been said to exhibit fungicidal, bactericidal and insecticidal actions, none of the substances of this group, which is described in, for example, U.S. Pat. No. 3,799,935, has become important in practice.
  • 2-Amino-4-trichloromethylpyridine can be obtained from 2-amino-4-picoline after appropriate protection of the amino group.
  • the amino group can be protected by, for example, reaction with phthalic anhydride. Halogenation of the 4-methyl-2-phthalimidopyridine with chlorine to give 2-phthalimido-4-trichloromethylpyridine can be carried out in the reaction mixture, without isolation of this compound; the protective group is then eliminated by hydrolysis, ethanolamine having proven useful for this reaction.
  • a solvent is advantageous to use.
  • suitable solvents are aromatics, such as benzene, toluene or xylene, aliphatic hydrocarbons, substituted aromatics, such as nitrobenzene or dichlorobenzene, and other halohydrocarbons, such as tetrachloroethane.
  • the water formed is advantageously removed by azeotropic distillation. The reaction takes place at from 50° to 250° C., preferably from 100° to 180° C. If halogenation is to be carried out without isolating the intermediate, a solvent suitable for the halogenation is advantageously employed from the outset.
  • Chlorobenzene and dichlorobenzene are preferred, but, for example, nitrobenzene may also be used.
  • a free radical former such as azobisisobutyronitrile, is advantageously added, in an amount of from 0.1 to 10%, preferably from 0.5 to 1%, based on the compound being chlorinated.
  • the reaction may also be accelerated with aid of a UV light source, in the usual manner. Chlorination is carried out at from 50° to 250° C., preferably from 120° to 160° C.
  • the hydrolysis is advantageously effected by the method described in German Laid-Open Application DOS No. 3,319,650.
  • ethanolamine for the hydrolysis, it is advisable to use as the solvent an excess of ethanolamine, water, an alcohol, such as ethanol, propanol or methylglycol, a ketone such as acetone, a chlorohydrocarbon, such as chloroform or an ether such as diethyl ether.
  • An excess of ethanolamine, ethanol or propanol is preferred.
  • the preferred temperature range for the hydrolysis is from -10° to 30° C.
  • nitrification rate of ammonium sulfate (taken as 100% or 1.0)
  • b nitrification rate of ammonium sulfate+nitrification inhibitor

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Soil Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
US06/838,780 1985-03-19 1986-03-12 2-amino-4-trichloromethylpyridine and its preparation Expired - Fee Related US4699983A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3509860 1985-03-19
DE19853509860 DE3509860A1 (de) 1985-03-19 1985-03-19 2-amino-4-trichlormethyl-pyridin, verfahren zu seiner herstellung und seine verwendung als nitrifikationshemmer

Publications (1)

Publication Number Publication Date
US4699983A true US4699983A (en) 1987-10-13

Family

ID=6265674

Family Applications (1)

Application Number Title Priority Date Filing Date
US06/838,780 Expired - Fee Related US4699983A (en) 1985-03-19 1986-03-12 2-amino-4-trichloromethylpyridine and its preparation

Country Status (6)

Country Link
US (1) US4699983A (da)
EP (1) EP0196522B1 (da)
JP (1) JPS61233671A (da)
CA (1) CA1254572A (da)
DE (2) DE3509860A1 (da)
DK (1) DK163504C (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5216171A (en) * 1990-04-23 1993-06-01 Basf Aktiengesellschaft 2-amino-4-trichloropyridine derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3135594A (en) * 1961-09-01 1964-06-02 Dow Chemical Co Method and product for treating soil to suppress the nitrification of ammonium nitrogen therein
US3682936A (en) * 1970-10-02 1972-08-08 Dow Chemical Co Certain 6-(trifluoromethyl)-pyridinols

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3787420A (en) * 1969-03-17 1974-01-22 Dow Chemical Co Cyanoalkoxy(trifluoromethyl)pyridines
US3799935A (en) * 1972-10-10 1974-03-26 Dow Chemical Co Substituted aminohalo-pyridines
US4154835A (en) * 1977-10-12 1979-05-15 Merck & Co., Inc. Anthelmintic imidazo [1,2-a] pyridines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3135594A (en) * 1961-09-01 1964-06-02 Dow Chemical Co Method and product for treating soil to suppress the nitrification of ammonium nitrogen therein
US3682936A (en) * 1970-10-02 1972-08-08 Dow Chemical Co Certain 6-(trifluoromethyl)-pyridinols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5216171A (en) * 1990-04-23 1993-06-01 Basf Aktiengesellschaft 2-amino-4-trichloropyridine derivatives

Also Published As

Publication number Publication date
JPS61233671A (ja) 1986-10-17
EP0196522B1 (de) 1989-07-12
DK163504B (da) 1992-03-09
DK163504C (da) 1992-07-27
EP0196522A1 (de) 1986-10-08
CA1254572A (en) 1989-05-23
DE3509860A1 (de) 1986-09-25
DK123886D0 (da) 1986-03-18
DE3664324D1 (en) 1989-08-17
DK123886A (da) 1986-09-20

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Owner name: BASF AKTIENGESELLSCHAFT, 6700 LUDWIGSHAFEN, RHEINL

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:HAGEN, HELMUT;ZIEGLER, HANS;KOHLER, ROLF-DIETER;AND OTHERS;REEL/FRAME:004710/0922

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